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The top boating charters in Upper Keys

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Step aboard Singing Reel Charters, a classic 1971 Hatteras Sportfish Convertible—beautifully restored and fully outfitted for unforgettable adventures in Islamorada. 

Singing Reel Charters

License to Chill Yacht Charters invites you to experience the magic of life on the water aboard a beautifully maintained 55’ Californian Cockpit Motor Yacht, based in stunning Key Largo. 

License to Chill Yacht Charters

Experience the best of Islamorada with Seas 2 Trees Outdoors, LLC aboard a sleek 2020 Yellowfin Yachts 36 Offshore Center Console. 

Seas 2 Trees Outdoors, LLC

Set sail on an unforgettable adventure with Aloha Boat Charters, a premium 2022 Sea Hunt Gamefish 27 Center Console based in Key Largo. 

Aloha Boat Charters

The Operator, Aquablue Adventures Fun Boat Charters & Tours, specializes in Islamorada Sandbar parties, Sunset cruises, Snorkeling, Sightseeing, Tarpon/Shark Feeding, or Bar Hop Booze Cruise. 

Sun & Fun Large Group Pontoon + Add-on Boats

Easy Livin Charter is a 2024 Key West 250BR center console bay boat based out of Islamorada that can comfortably handle up to six guests. 

Easy Livin Charter

Experience the best of the Florida Keys with a private charter departing from beautiful Key Largo, Florida - or, if you're staying in Islamorada, let us know in your message and we may be able to accommodate a Islamorada pickup!


SeaEO V - Key Largo/ Islamorada - Luxury Boat

A favorite boat in the fleet, physically large enough to seat 12 passengers (but restricted to 6 maximum), is the 2018 Nautic Star Deck boat (based out of Islamorada). 

Sporty, Spacious Deckboat With Lots Of Shade

Step aboard Reel Morada, a freshly restored 2004 Contender 25T Center Console, now better than ever for unforgettable adventures out of Islamorada! 

Reel Morada

Step aboard Key Largo Tiki Tours, a 2023 A & M Boat Works 34’ Catamaran Tiki Boat, and set off on an unforgettable adventure in the stunning waters of Key Largo. 

Upper Keys: 46 boats available

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Upper Keys: 46 boats available